Boylan was the long-time record producer for Linda Ronstadt, also arranging and playing guitar or piano on select tracks. He hired her backup band which included Don Henley, helping to start his career. Other artists whose records were produced by Boylan included Odetta, Ricky Nelson, Carly Simon, and the Charlie Daniels Band.

Boylan formed his own music company, Great Eastern Music, in 1986. In 1990, he produced the first Simpsons album, The Simpsons Sing the Blues. He produced other cartoon and children's themed albums, including the Simpsons' Yellow Album and three for the Chipmunks (Urban Chipmunk, Chipmunks in Low Places and A Very Merry Chipmunk). Boylan has also produced film soundtracks, including Cry-Baby, My Stepmother Is an Alien, and Hope Floats.